Journal of Organic Chemistry 2008-01-18

Trimethylsilyl trifluoromethanesulfonate (TMSOTf) assisted facile deprotection of N,O-acetonides.

Kevin W C Poon, Kimberly M Lovell, Kendra N Dresner, Apurba Datta

Index: J. Org. Chem. 73(2) , 752-5, (2008)

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Abstract

Employing TMSOTf as an easily available reagent, we have developed a mild and efficient method for the deprotection of both terminal and internal N,0-acetonide functionalities. Various regularly used protecting groups and common organic functional moieties were found to be unaffected by the described reaction conditions. In a few representative examples, the present method was also extended to deprotect acetonides obtained from 1,2-, and 1,3-terminal diols. The acetonide deprotection protocol described herein is expected to be a useful addition to the presently available methods for performing the above transformation.